Electrooxidative Synthesis of Bis- and Oligoarenes

• Applicant: Professor Dr. Siegfried R. Waldvogel
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2015 to 2019
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 286171883

In this joint project, the mechanism and scope of a new electrooxidative biaryl coupling of substituted arenes will be explored and defined. This electrochemical approach has the advantage that no leaving functionalities are required for biaryl cross-coupling. Since no reagent waste is formed in this reagent- and metal-free electroorganic process, a highly sustainable synthetic method will be established. The use of electricity and solvent effects to direct the selectivity of the cross-coupling creates a cutting-edge technique in contemporary organic synthesis. This innovative cross-coupling concept based on the decoupling of nucleophilicity and oxidation potential the substrates can be considered as a new type of umpolung and is the source of the outstanding coupling selectivity. The efficiency of this new methodology will be exploited for the efficient and modular synthesis of mimetics for a-helices based on teraryl and quateraryl architectures. The strategy involves a complementary combination of modern metal-catalyzed steps as well as electrosynthetic transformations which do not require leaving functionalities and provide a direct and sustainable access to such entities.

• DFG Programme: Research Grants
• International Connection: Austria
• Co-Investigator: Professor Dr. Rolf Breinbauer